Yarn conditioning process and composition therefor



Patented Aug. 4, 1942 YARN CONDITIONING PROCESS AND COM- POSITION THEREFOR Joseph B. Dickey and James G. Mel Wally, Roch ester, N. Y., assignorsrto, Eastman am: Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application August 15, 1939, Serial No. 290,320

3 Claims. (Cl. 252-83) This invention relates to the conditioning of textile yarns and more particularly to the lubri cation of filaments and yarns composed of organic derivatives of cellulose such as cellulose acetate, cellulose propionate, cellulose acetate propionate, and cellulose acetate butyrate. to render them more amenable to textile operations such as weaving, knitting and the like.

As is well known in the manufacture of yarns. particularly those composed of or containing cellulose organic derivatives, it is necessary to treat the yarn in order to reduce the tendency toward breakage of the individual filaments or fibers when they are subjected to various mechanical strains and to lubricate the yarn in order to facilitate handling in such operations as spinning, twisting, winding and reeling. It is also necessary to treat yarn to adapt it for use as warp or filling or for the manufacture of various types of knitted fabrics.

This invention has as its principal object to provide an entirely new class of yarn conditioning agents which are particularly adapted for the lubrication of yarns composed of or containing organic derivatives of cellulose. A further object is to provide lubricating formulas whichcan be readily removed from the yarns by the usual scour baths. Another object is to provide an improved type of yarn which is especially amenable to textile operations including weaving, spinning, knitting and the like. Other objects will appear hereinafter. y

These objects are accomplished by the following invention which, in its broader aspects, com- I prises the discovery that ketones prepared by reacting certain aromatic hydrocarbons such as benzene, naphthalene, diphenyl, triphenyl, anthracene, dibenzofuran, furan, thiophene. acenaphthene, etc., in substituted or unsubstituted form, with naphthenic acid chlorides prepared by reacting a naphthenic acid or, mixture of naphthenic acids with an acid chloride-forming reagent such as thionyl chloride, phosphorus pentachloride, phosphorus trichloride, oxalyl chloride, benzoyl chloride. etc., may be used as yarn lubricating agents. In preparing ketones of phenols any suitable modification of the Friedel-Crafts reaction, such as the Frees rearrangement, may be employed. if desired. By the above reference to naphthenic acids we refer to acids such as those described in chapter 48 of the text by Carlton Ellis entitled "The Chemistry of Petroleum Derivatives." first edition (1934), published by the Chemical Catalogue Company, New York, New York.

The ketones thus prepared may be employed as yarn treating agents alone, or in conjunction with other known textile lubricants such as animal, mineral, or vegetable oils and/or. various yarn solvent or softening agents such as glycerine, ethylene glycol, polyethylene glycols and their ethers and esters, and similar agents. The oil ingredient of such compounded yarn treating compositions may include sulphonated or un-. sulphonated oils. phosphated or phosphited blown and unblown vegetable and animal oils and similar materials.

PREPARATION OF COMPOUNDS Pusan NAPHTHENYL Karena Three hundred g. benzene, 6'1 g. aluminum I chloride and 73 g. naphthenic acid chloride are heated with stirring on a steam bath for 10 hours or until no more hydrogen chloride is evolved. When the reaction mixture is cool, it is poured on ice, separated. washed with 5% hydrochloric acid followed by water and distilled. There is obtained an excellent yield of phenyl naphthenyl ketone boiling at -300/l mm.

Tmmwi. NAPHTHENYL KETONE Seventeen g. thiophene are dissolved in 150 cc. benzene with 40' g. naphthenic acid chloride. There is then added withstirring 26 g. titanium tetrachloride and the reaction is completed by warming. When cool the" reaction product is poured onto ice and then worked up as in the preceding paragraph. There is obtained an excellent yield. The resulting thienyl naphthenyl ketone boils at -300/l mm.

PYaaYL NAPHTHENYL Karena 0- AND P-HYDaOXYPHENYLNAPHTHENYL Karena Three hundred and seventy-four g. of aluminum chloride and 400 cc. carbon disulilde are placed in a reaction flask and 500 g. phenylnapnthonate are added. The reaction begins andh'e at ketone boiling at 200290/ mm.

/ Three hundred cc. carbon bisulflde, 67 g. aluminum chloride, 75 g. naphthenic acid chloride and 33 g. naphthalene are allowed to react at room temperature for twenty hours. The reaction product is workedup as in the preceding paragraph. There is obtained a good yield of naphthyl naphthenyl ketone.

In a similar manner, trlphenyl, anthracene, diphenyl ether, benzanthrene, acenaphthene, anisole, carbazole, dibenzo fur-an, etc., are reacted, and the corresponding compounds obtained.

Narnrnmn-Xxnrn Ksrrona i-kgf dry mixed xylene is heated on a steam bath for 24 hours with.400 g. aluminum chloride and 250 g. mixed naphthenic acids. The product is poured onto ice and treate with 5% hydrochloric acid. When hydrolysis is complete the xylene-ketone layer is separated from the water and distilled under reduced pressure. There is obtained an 80-85% yield of naphthenyl-xylyl Inaccordance with the invention these com- I pounds may be applied directly to the yarn durxylylnaphthenylketone (mixed)-- 99-1 Alkylated naphthalene naphthenylketone- 5-30 This mixture is applied to textile materials such as silk, wool, viscose. cellulose acetate, etc., as described in Example 1. If the yarn is intended primarily for knitting, the amount of condition- 5 ing liquid applied may vary between 2 by weight of the yarn, and if for weaving, the amount of liquid applied may vary between 1 and 5% by weight of the yarn. Cellulose acetate filaments or fibers treated as described above are I quite soft and pliable and give improved results in various textile operations such as weaving, knitting, etc.

materials such as cellulose acetate, viscose, silk,

-wool, etc. from a benzene solution as in Example 1. The benzene is removed by passing the ma- 0 terials through a suitable drying cabinet. If the yarn is intended primarily for knitting, the

amount of conditioning liquid'applied may vary from 2-25% by weighfof the yarn. If the yarn is intended for weaving, the amount of condition- 25 ing'liquid applied may vary between 1 and 5% by weight of the yarn.

Other examples of yarn conditioning compositions which ma be applied to various types cellulose organic acid esters in accordance with our invention and which render such yarns especially well adapted for various textile operations such as weaving, knitting, are as follows:

ing or after spinning, or may be added in the Example 4 spinning solution itself. We have found that a 1 PM these compounds have excep ion l' w 4o Naphthenyi dlphenyl ketone 75-99 1 bflcate textile r m particularly th {l-Methoxyethylsuccinate r posed of or containing organic derivatives of cellulose such as cellulose vacetate. 05111110, Example 5 acetate propionate, cellulose acetate b tyrate,. and i320 like. a; prevhilously indicate'd. tlae y with? a: may be employed connection th e T tr usual yam lubricating materlalb, such as e, ahydmmrmryuormal 59-30 mineral oil, and blown and unblown, dry- Example 6 ing and semi-drying, vegetable and animal oils, 9 1 wand waxw a Naphthenyl phenahthrene 1.10 In the following examples and description, we 310W! 99-90 have set forth several of the preferred embodimentsof our invention, but they'are included I 3 7 merely for purposes of illustration and not as a 4drmhemmbhthwl ketone 14 limitation Heat's-foot oil- 99.

Our invention will he more readily understood by reference to the following examples in which sample 8 typical applications of the invention are set forth.

, ample 1 2.5-dihydroxy phenylnaphthenylketone" 1-15 Blown neat's-foct oil. 99-85 Phenyl naphthenyl ketone'is applied to textile materials- (all?y wool, cotton, cellulose acetate. mp 9 viscose, etc.) means of a bath, wick, roller.

j spray, etc., to facilitate their knitting, weaving, ketone f spinning, and the like. If the yarn is intended r M primarily for knitting. the amount of condition- Exampl 10 1 ing liquidapplied may vary from 2 to 25% by Y e weight of" the yarn. n the yarn is intended pri- Blown sperm oil 1 fillsilliy toruwgaving. the 8350M flfizgg s t Ethanolamlne acetate prBBEiQE n :5

q appemayvary tween %by weight of the yam I 7o ip nyl dibenzoylfumn ketone 5 Parts Sperm oil 0.30 olive on 1-99 Butyinaphthenate 5-20 of yarns, particularly those composed of or containing cellulose acetate, cellulose acetate proplonate, cellulose acetate butyrate, and similar Example 12 l 1 Parts Mineral oil 30 Naphthenyl p-phenoxy phenylketone 20 Blown neats-foot oil 40 Oleyl alcohol 5 Tetrahydrofurfuryltetrahydrofuroate 5 Example 13 Mineral "oil 70-50 Oleic acid 1-25 p-Aminophenylnaphthenyl ketone 29-25 Example 14 Blown sperm oil 25 Blown olive oil 25 Blown neats-foot oil 25 Sodium sulfate. 2 Oleic acid 22-13 Suli'onated castor oil 1-10 Example 15 fi-Methoxyethyladipate 20 Blown neat's-foot oil 30 Sulfonated olive oil Mineral oil 10 Oleic acid 10 Phenylnaphthenyl ketone l0 Ethanol amine 3 Water 7 Example 16 A twenty per cent solution of cellulose acetate in acetone in which is incorporated 1-25% by weight of the cellulose acetate of phenyl naphthenyl ketone is extruded through fine orifices into an evaporative atmosphere. The filaments thus produced are wound or twisted and wound. Yarns produced from filaments thus prepared are pliable and suitable for knitting.

Any of the above lubricants may be applied to the yarn by means of a bath, wick, spray, roller, pad or any suitable means. The amount of the lubricant applied may vary between 1% and 25% by weight of the yarn treated.

Although in the above examples, we have referredv primarily to yarn treating compositions containing only the lubricating compounds which are the specific subject of this application, together with an oil, other ingredients such as solvents, non-solvents, emulsifying agents, blending agents and the like, may be added within the scope of our invention. Likewise, various dyes or other coloring matter may be included in case it is desired to fugitively or permanently tint or dye the material undergoing treatment.

Although we have found it convenient to illustrate our invention by reference to. compositions containing specific percentages oi the various ingredients, these percentages may vary widely depending upon the particular purpose for which the composition is intended.

While we have described our invention with particular reference to the treatment of yarns composed of organic derivatives of cellulose such as cellulose acetate, the lubricating formulas described herein are applicable to the lubrication of many other types of cellulose derivative yarns such as those composed of or containing cellulose propionate, cellulose butyrate, cellulose acetate propionate and cellulose acetate butyrate, ethyl, methyl and benzyl celluloses, as well as to the lubrication of silk, wool, cotton, viscose and other natural or synthetic materials.

The term yarn" as used herein and in the claims is to be understood as including a single filament,a plurality of filaments associated into the form of a thread, either of high or low twist, single or multiple threads associated or twisted together, composite threads composed of a mixture of natural and artificial filaments or a composite thread formed by twisting together individual strands of natural or artificial materials, as well as out staple fibers produced from natural and/or artificial filaments or threads and spun yarn produced from such staple fibers.

The compositions described herein have been found to possess exceptional ability to lubricate and condition cellulose organic derivatives and other yarns for use in various textile operations such as weaving, knitting, twisting, spinning and the like. Due to the solubility in water of the compositions, they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths. By employing the yarn lubricating agents herein described, one is enabled to obtain highly satisfactory results in the manufacture of yarns and woven fabrics of various kinds.

What we claim is:

1. The process of conditioning textile yarns composed of or containing organioderivatives of cellulose to render them more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a yarn lubricating composition containing as its essential lubricating component xylyl naphthenyl ketone.

2. Textile yarns composed of or containing organic derivatives of cellulose which are amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a lubricant containing as its essential lubricating component xylyl naphthenyl ketone.

3. A textile yarmlubricating composition, the essential lubricating component of which is xylyl naphthenyl ketone.

JOSEPH B. DICKEY. JAMIES G. MCNALLY. 

